


Hi Jay!

by chilly83



Category: Chicago PD (TV)
Genre: Co-workers, Fluff, Fluff and Humor, Humor, Relationship Reveal, Secret Relationship, Softball game, Upstead
Language: English
Status: Completed
Published: 2020-05-16
Updated: 2020-05-16
Packaged: 2021-03-03 04:01:14
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,678
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24208618
Author URL: https://archiveofourown.org/users/chilly83/pseuds/chilly83
Summary: Hailey never noticed how many women Jay was friends with until one day at a softball tournament.No angst, just fun!
Relationships: Jay Halstead & Hailey Upton, Jay Halstead/Hailey Upton
Comments: 12
Kudos: 120
Collections: Hailey and Jay One Shots





	Hi Jay!

**Author's Note:**

> Hi all! Thanks again for all the support through my other fics. I love reading about how much you guys are enjoying them! Normally, I would be preparing for a 2 day softball tournament my husband was playing in but Corona has made that impossible. So instead, I decided to channel all the fun and camaraderie into a fun little Upstead one shot. I hope you enjoy!
> 
> My inspiration for this was Jay season 1 when he had a bit of a reputation for being a play boy. It is so different from the mature Jay that Hailey has always known and I wanted to play with that a little bit.

This had all started out as an attempt to raise some money for a local Chicago food bank. Hermann had come up with the idea when 51 responded to a call at their warehouse. While they were able to put the fire out quickly before too much damage was done, Hermann wanted to do more. That’s how Hailey and Vanessa ended up here, setting up canopy tents at 7 am on a hot summer weekend in Chicago. 

Hermann had figured that some kind of sporting event would bring in lots of spectators and boy was he right. What started as a friendly game of softball at a local field between 2 teams consisting of a group of police officers, firemen and staff from Med had turned into an all-day softball tournament. Once Hermann began advertising the event at Molly’s, selling tickets to the event with 100% proceeds going to the charity, a local newspaper picked up the story. They featured an article on the food bank and how the Station 51 came into it’s orbit.

After the newspaper printed the story, Hermann started getting overwhelmed with calls. They had sold out of tickets very quickly between the flyers at Molly’s and the food bank, but there were hundreds of people still calling trying to get their hands on some. He was also getting calls from other first responders hoping to get on to one of the teams. As the list kept growing, Hermann realized he had enough people wanting to play to make it into a tournament, and enough people wanting to watch to make it into an event. 

He reached out to Trudy, knowing that there was not a single person in the city of Chicago that didn’t owe her a favor, and was able to secure a permit and a large park with 2 different baseball fields on it. This would allow for 2 games to go at a time to help move the games along. He also contacted food trucks and worked out an arrangement for them to sell food at the event to keep the spectators well fed and hydrated, with the food trucks agreeing to donate a percentage of their earnings to the food bank. 

A local event planning company offered to donate multiple canopies that could be used to set up shade for the teams to rest in between games and additional bleacher seating to accommodate the crowds. The event was advertised as family friendly, encouraging guests to bring lawn chairs, blankets, whatever they wanted to enjoy a fun day at the park. He also relied on friends and family to set up the park on game day. 

Since Hailey and Vanessa were not playing on a team, they volunteered to show up early to help set up tents and check in teams. Hailey was finding it harder and harder to get out of bed on her days off; she had recently acquired a new appreciation for lazy morning in bed with her partner. But when she was asked to help with setup, she couldn’t turn Stella down. 

Once they finished setting up the tents for the teams, the players began arriving to check in. As she was checking them in, she noticed lots of first responders that she had never seen before but were certainly easy on the eyes, and they seemed to take notice of her as well. As Jay approached the tent to check in, he also noticed how Hailey was trying to move the other players along as they tried in vain to flirt with her. At this point, Vanessa and Will were the only ones that knew about the relationship, so there was not much he could do to shoo the men away but that didn’t mean he couldn’t mess with Hailey a little bit. 

“So,” he said as he was signing the liability waiver, “how worried should I be about all these guys?” He smugly asked. Before Hailey could answer, the conversation was interrupted by a couple of nurses from Med.

“Hi Jay!” They said in unison as they waved to him. Jay smiled and nodded at the women as they walked by. 

“Seriously. Is how I play today going to impact how attractive you find me?”

“I find you attractive?” Hailey joked back with a smirk on her face.

“Hi Jay!” Another lady called out as she walked by the check-in tent with some friends. He again waved back and smiled.

“I guess you have never come right out and said it. But” he said as he set down the clipboard and took a step closer “I have caught you a few times” he stepped closer again, leaned in and whispered, “checking me out in the shower.” Hailey tried to contain her blush.

“Oh that?” She said as she put a hand on his chest to push him back slightly. “That’s just me being a good partner. Making sure you don’t slip and fall.”

“Hi Jay!” Another called out with a flirtatious wave. Hailey started to notice that a lot of women had walked by to say hi to Jay in the 5 minutes he had been at the park. She realized she didn’t know every person that Jay knew, but still. 

“Hey!” Jay responded as he waved hi back to the woman.

“Well” Jay said as he began to walk away from her “if you aren’t busy later, I will definitely be needing a spotter in the shower again. You know, for safety reasons.” He said as he winked at her and walked away. She shook her head and again rolled her eyes at her partner.

As the games began, Hailey finally had the chance to sit with some other friends and watch from the stands. Jay’s team was one of the first to play, so her and Vanessa made their way over to Will, who was watching while he waited for his game. 

“Did you and Jay purposely sign up for different teams?” Vanessa asked, wondering why the two brothers were not on the same team.

“It’s only fair to spread out the talent. Can’t have one team dominating the whole tournament.” Will joked to the ladies. 

Hailey noticed then that there was a woman, a different one from the first 4, that was standing against the fence talking to Jay. Jay was standing in the on-deck circle, taking practice swings with his bat, and seemingly having a friendly conversation back with the woman. Hailey could not help the feeling of jealousy that began to creep up on her. She knew Jay was a charming man with a smile that could bring women to their knees, not to mention that body. 

Hailey shook her head as her mind began to wander to less family friendly thoughts and tried to refocus. Jay’s hot, people notice, move on, she told herself as she tried to shake off her insecurities. In that moment, all Hailey could think to do was walk over to Jay and plant a kiss on him, letting the women know that he was taken, but she resisted the urge. She opted instead to push the jealous thoughts out of her mind and enjoy the day.

It was easier said than done. 

+++++++++

Throughout the day Hailey couldn't help but notice how many women stopped by the dugout to say hi to Jay. Jay, for his part, seemed completely oblivious to the numerous women who were trying to get his attention. Some just waved and said hi, some started conversations with him. A couple did the whole twirl their hair and toss it over their shoulders’ thing, and a couple of bold ladies went as far as touching Jay's arm while laughing at whatever he just said. 

Hailey had been able to brush it all off and enjoy herself until just before the last game. The team intelligence was on had made it to the final game. The whole unit was under the team’s canopy joking around while those playing began to change into their cleats. 

"I watched these guys play in the second round. Think you can handle your brother's bat?" Adam joked to Jay. Will had a surprisingly powerful bat and had cleared the bases a few times.

"If he hits them to left field, I'll be all over it". Jay chuckled.

"Looks like your fan club is already setting up." Kevin joked to Jay while motioning over to a group of nurses who were setting up their folding chairs near the dugout. 

"Pretty sure they are Team Will." Jay said as the team started to gather their bags move into the dugout. Jay fumbled with his bag momentarily, so he had an excuse to hang back with Hailey. Vanessa made her way over to their seats on the bleachers letting Hailey and Jay have their privacy. 

"He's right." Hailey said with a head tilt. "They are _your_ cheerleaders."

"Pretty sure that's not how it works." Jay said with a laugh. "Cheerleaders cheer for teams, not players."

"I’m not sure they got the memo.". Hailey retorted, unintentionally giving Jay the side eye. 

"Wait." Jay said as he rose to his feet. "Are you jealous?" He asked while trying not to laugh.

"No.” She said looking him in the eye. “NO!" she said a second time hoping to convince him. "I'm just saying, they aren't out there cheering for the team, they are cheering for you."

"What is the difference?" Jay asked sincerely not getting the difference. 

"I'm cheering for the team. They only cheer when you make a play or go up to bat.". Hailey explained. 

"I don't think it makes a difference. In the end they want the team to win.". Jay reasoned playfully. He really should not be this amused with Hailey's jealousy but it's something he never thought he would see. 

"Ok Halstead. You're right. It's the same." She says with a smirk. Jay finds himself a little concerned with how easily she gave up. 

"Good luck." She says as she pats him on the back and turns to leave. 

" I don't need luck! I've got a whole cheering section!" Jay yelled out as he watched Hailey walk away. 

+++++++++++++

As the final game progressed, Jay became more aware of what Hailey was talking about. He started to notice the cheers that seemed to be directed at him rather than the team. He tried his best to ignore it and focus on the game. 

"Alright Halstead you got this." Hailey yelled as Will walked up to the plate. 

It was the second inning; the bases were loaded and Will was up to bat. Jay was shocked at how openly Hailey was cheering for him. She had cheered throughout all the games, but never actually singling him out by name. Jay watched as Will swung at the first pitch and missed. When he heard Hailey yell out again, he suddenly realized that the cheers were not directed at him, they were for Will.

"Come on Halstead. Shake it off. You got this."

"Upton!" Adam yelled from the pitcher's mound. "What the hell are you doing!?!"

"I'm cheering for my favorite Halstead!" She yelled back. She laughed as she saw Jay throw his hands up in defeat.

"Jay, get your girl!" Kevin yelled back at Jay from first base. 

After the team laughed off the exchange, Adam focused himself for the next pitch. As soon as it left his hand, he knew it was bad. 

Will swung and the crack that the bat made when it hit the ball brought the crowd to their feet. Jay ran as fast as he could back, back, back until there was nowhere else to go. He jumped on the fence in an effort to gain more height as he reached up to catch the ball, falling short a couple of inches as it cleared over the fence. 

Will trotted around the diamond, fists pumping in victory as he relished in the crowd's cheers. 

"He only hits homeruns cause he can't run!". Jay yells out at his brother as he rounds second. 

"Never had to practice running since I can hit!" Will yelled back at his brother as he completed his victory lap to home plate, being sure to shoot Hailey a wide grin as he went back to his dug out. 

Luckily for Hailey, the next batter up was the third out and Jay's team had a chance to even out the score. 

As the team started batting, Hailey continued to cheer with the same level of enthusiasm she had throughout the whole tournament. She clapped along and yelled out words of encouragement as the players came up to bat. 

When Jay came up to bat, the ladies that had set up near the dugout began cheering him on. 

"Alright Jay! Let's even this up."

"You can do it Jay." He heard them yell to him. Jay turned to look at the only cheerleader that matter to him: Hailey. 

"Come on Halstead! Get your head in the game!" Hailey yelled out to him when she saw him look back to her. 

“She ain’t talking to you, Jay!” April yelled out to the detective. Jay laughed as he stepped up to the plate.

"If I get a home run, do I go back to being your favorite Halstead?" He yelled out at her. 

"Who said you ever were her favorite Halstead?" He heard Will yell from third base. Jay shook off the joke and got into his stance. 

As he watches Ethan release the ball from his hands, Jay took one step forward and put all his weight into his swing. Once again, the crowd was brought to their feet at the sound of the bat connecting with the ball. He began to run as he watched the ball clear over the fence, signaling a home run. 

As he rounded third base, he turned to Will and threw his arms up in the air as if calling out his brother. Once he crossed home plate, he headed for the dugout and was greeted with high fives and hugs from his team. 

Jay promptly exited the dugout and trotted over to the stands. 

"You were right.". Jay said as he approached Hailey on the stands. 

"I'm right about so much Jay. You have to be more specific.". Hailey shot back at Jay as he began to climb the stands. 

"It's different. Cheering for the team and cheering for a player.". He said smugly as he reached where they were sitting. “I definitely noticed the difference.”

Hailey laughed at him playfully and looked over to the nurses who were sitting by the dugout.

“Make sure you thank your fans for all the support.” Hailey said, motioning over to the group.

Just then, she was caught off guard when Jay leaned in and pecked her on the lips.

“I’m only worried about one cheerleader.” He said as he placed a hand behind her head to pull her in for another kiss. The moment was broken when they heard the teams on the field beginning to cheer for them. Any other time both Jay and Hailey would have been mortified by all the attention that was being thrown their way as they tried to share a moment, but for some reason, this time they were able to laugh it off.

“It’s about time!” They heard someone yell from the field. 

“Get it girl!” They heard from another direction. Hailey blushed as she brought her hands up to cover her face from the embarrassment. She spread her fingers out and shyly peeked out to gauge Jay’s reaction. 

“Alright, alright. Show’s over.” Jay yelled as he got up and tried to shoo away the spectators. “Sorry. I couldn’t help myself.” He said as he began to climb down the stands.

“You can’t buy my love with kisses Jay!” Hailey yelled out to him as he jogged back to the dugout, making sure to wave at the crowd as he did.

“We’ll see about that!” He yelled back, excited to accept the challenge. 

**Author's Note:**

> Thanks for reading! I hope you enjoyed! Stay safe out there! I currently have no ideas for any new fics but I am hoping to get some inspiration soon!


End file.
